The Bet - Chapter 12 (Wednesday – week 2 Part 1)

The Bet
by Karen Singer

Chapter 12 (Wednesday – week 2 Part 1)

Sharp little pinpricks to his private area slowly seeped their way into his dreams, increasing in strength. He groaned for the hundredth time and came partially awake. He hadn’t slept hardly at all because of those pinpricks. He rolled over on his blow-up mattress as best he could since his diapers were so swollen that maneuvering was difficult – especially now with the chastity device she had locked onto him. That by itself was a nightmare to deal with – even when it wasn’t hurting him. Finding a comfortable position to lay in was even more challenging.
The pain of the pinpricks died away and he fell blissfully back to sleep, but only for a little while. His alarm clock began blaring loud music. He jolted back out of his sleep with a start, trying to comprehend the commotion. No, the device wasn’t hurting him just then. Finally he realized his alarm was signaling that it was time to get up. He pounded his fist on the bed and rolled into another semi-comfortable position, again. But the loud music was still there. Cursing under his breath, he got to his feet and turned the music off.
He stood there for a while just looking at the floor, totally fogged out, not even trying to make sense of anything. His diapers felt like one huge solid ball between his legs. But that was beginning to feel normal to him now. He wanted to go back to bed. To sleep, for a week – at least. But there was some reason why he couldn’t. What was it? Why couldn’t he go back to sleep? Finally the reason seeped through. Oh yeah, it was time for another baby bottle. Then he had to get ready for work. Ugh!
Walking into the kitchen was more like swinging one leg after another around the huge bulk of his diapers. But that too was feeling more normal to him. He didn’t even think about it. He opened his refrigerator, Mel had restocked it again yesterday. Way too many baby bottles – and nothing else. He grabbed one at random and put it into his mouth as he headed back to his mattress. Her lousy tea again. He was so used to it that he didn’t give it another thought. He just laid back on his back and held it to his mouth like a baby and drank. He was very well used to that too. It was almost comforting now in a way. But he was too tired to realize it.
As he drank, the need to pee seeped partially into his brain, he let it loose without thinking about it, just as he had all night so he could get at least some sleep. He began concentrating on the feeling of the pee rushing out of him. It was better than concentrating on other things that might make those little pinpricks come back again. The feeling of peeing felt good just then. He relaxed and enjoyed it. But all too soon it was over. He couldn’t tell one bit of difference to his diapers. They were that wet.
His foggy brain woke up a bit more as his bottle finished. He carefully rolled to his feet and carried it back out to the kitchen. There was a collection of empty bottles on his counter. This made bottle number five. Way, way too many.
He went back into his bathroom to shave and brush his teeth, not sure if he wanted Mel to be early so she could change him sooner, or late so he could go back to sleep.

Mel poured herself a cup of coffee and took her first sip. Mmm, it tasted good. She just hoped it would wake her up quickly. She thought for the thousandth time about Chad. Had he slept well? Had he slept at all? Did the device she locked onto him hurt him too much? She had no answers. She had worried about him all night. But the only way she was going to get those answers was to go see him. That time was approaching. She took another sip of her coffee and started to get ready, only throwing on some jeans and a t-shirt. She would take her time getting ready for the office later.
She grabbed her keys and went over to his apartment, unlocking his door with her copy of the key. She heard water running in the bathroom. At least he was up. She went to see him.
Chad turned his head while he was shaving and saw Mel standing in his bathroom doorway watching him. He hadn’t heard her come in. He realized that going back to sleep was out of the picture now. She was just standing there watching him. “Good morning, Mistress,” he said.
“Good morning, Sissy,” she replied.
Chad went back to what he was doing. When he had finished shaving she took his onesie off of him and helped him get his diapers off again. When he was finally naked, Chad looked down. It was his first glimpse of the device she had put on him last night. It was all clear plastic, totally covering every bit of his penis. There were small slits in it for cleaning or to let his pee out, but touching himself was obviously impossible. The way it was molded, it held his cock firmly straight down so it couldn’t go in any other direction.
There was a band wrapped tightly around his balls and the base of his cock that held it tightly to him. He reached down and touched it. It felt hard. He could feel nothing of the touch of his finger from inside. As he looked closer, he could just see the tiny little jagged spikes that dug so painfully into his skin the moment he got any larger than he already was. He suddenly felt the start of the pinpricks from those spikes again and took his hand away. The thing was a nightmare. An absolute nightmare. Sighing, he looked up at Mel who had been watching him.
“Ok, enough, into the shower now and get cleaned up.”
While Chad was in the shower, she picked out the clothes she wanted him to wear for the day, then she found his purse on the living room floor where he had dropped it last night and carried it into the bathroom. It was heavy since it held all of his makeup. A short time later, Chad was again diapered with a fresh suppository up inside of him, and once again wearing his all-in-one girdle with pantyhose over it. The girdle compressed his chastity device against him tightly, but surprisingly it helped to hold it in place so it was really no problem there. The thing that he really wasn’t used to now was that the chastity device held his penis straight down – permanently. He wasn’t used to that and it felt strange. There was a bit of an extra bump in the front of his girdle now but it didn’t appear to be too bad at all.
Once again it was makeup time. But this time Mel began by showing him how to apply his eyeliner. This was by far the most difficult thing he had tried yet. Over and over again he tried but he couldn’t get the lines exactly right. Finally Mel said, “Close enough. Leave it and do your mascara and eye shadow now.” Chad did as he was told although he wasn’t happy about it. Obviously Mel was going to require him to wear the eyeliner to work too. Why? She had to know that he was still washing it all off as soon as he got there.
“Put another coat on the mascara,” she instructed him before he finished with it. “I want it to be a bit more visible today.”
The little pinpricks were suddenly back again. He paused in what he was doing to let them settle back down a bit before he was capable of continuing. Then he went back to making his mascara a bit heavier. He still had to wonder why she was bothering.
When it was time for him to get dressed, Mel handed him another of his male shirts, then the navy blue female slacks he had bought a few days ago. He wasn’t happy to see them at all, but he knew to expect them since she had fixed it so he couldn’t get at any of his male pants.
The biggest surprise of the day though, was when Mel handed him the low heeled pumps that he had worn all last night instead of his male shoes. The pinpricks suddenly came back in a major way, and they didn’t seem to want to go away this time. He set the shoes down on the floor, but he had to back away from them. The device was hurting him too much. He waited, desperately wanting the pain to die down. It did finally, but not much.
Mel watched as Chad tried to deal with the pain of the device. She knew she had to be patient and just let him learn to deal with it. In a way, she felt sorry for him but she wasn’t going to back down now – for any reason. She knew without a doubt that what he was going through now was critical.
Chad’s pain finally reached a level where he could tolerate it, some. He approached the shoes and slipped his left foot into one. The pain started to come back again. He had to push hard to get his foot all the way into the shoe since it was a bit tighter than he liked. The shoe was on and there was now a partial ring of fire against the base of his cock. He had to pause, desperately willing the pain to go away again, but it stayed. Fighting through it, he put the other shoe on.
He was now wearing women’s shoes to go to work in… they went right along with the women’s pants he was also wearing… which also went all too well with the pantyhose and the all in one girdle and the makeup and the purse he would be carrying later. He was going to have to go to work again dressed like this. Just thinking about his situation was fueling his sexual need in a major way. His cock was desperately trying to get hard where it obviously couldn’t. The little amount of swelling it was trying to do now had those miserable spikes firmly dug deeply into him, causing him immense pain. He grabbed at his crotch uselessly, prancing around the room half doubled over. Why did he have to be so turned on by all of this?
It took him four or five full minutes to even begin to get the pain under control. He dared not look down at his shoes again because every time he did it acted like a signal to start the pain all over again. He tried desperately to not think about his situation, but that was impossible. Worse, even the pain was now fueling his need. Eventually, he was able to come to grips with what was left of the pain… at least enough to function.
Mel had stood back and watched the whole process with a resolute expression on her face. Chad had to know that despite the pain that he felt, she wasn’t going to release him. When it looked like he was finally recovered enough, she left him to prepare his diaper bag for the day. As she was putting the two fresh bottles in it, she glanced at the time, it was getting late. Too late. There wasn’t enough time left to give him another bottle before he left.
Chad had finally come out of the bathroom and was waiting in his living room for her. “You forgot your purse,” she said to him. He seemed to sigh a bit but he turned around to go get it. “Make sure you bring all your makeup with you today,” she called behind him. She got no response, but when he came back out again, she could see that his purse was still fairly full and heavy. She handed him his diaper bag. “Have a good day,” she told him as she opened his door for him.
He looked at her with an almost menacing expression on his face for a few moments before he turned and walked outside. As he walked further away she said softly, “And good luck!” She could have been soft on him this morning and not made him wear anything new after putting the chastity device on him, but she had been a lawyer too long. She looked at it the same as if she were grilling a hostile witness. You could be soft or hard and change your tactics in mid-stream, but once you made a little chink in their armor, not matter what, you never backed down. You just kept hammering at them till they finally cracked.

Chad forced himself to take one step after another as he headed down to his car. Just walking outside like he was had caused another flare up of the pain, but he was dealing with it better now. He got into his car and set his bags down on the passenger seat and closed his car door. He closed his eyes, trying to will the pain to go away. He sat there like that for a while before he was finally able to do anything else.
When he finally felt strong enough to drive, he realized that he didn’t have his keys, they were in his purse. He had to dig through tons of makeup to find them, a major nuisance. But finally he was able to start his car and drive straight to work. He didn’t have time to stop for breakfast on the way.
When he got there, he automatically reached into his console and pulled out the socks he had hidden there. It was difficult to do in the car, but he pulled one shoe off and slipped one of the socks on. Then he tried to put his shoe back on. It wouldn’t go. The shoe was simply too tight and his socks were just too thick. There was no way. But he continued to struggle anyway. The sudden loud knocking on his car door window made him jump, scared out of his wits. He turned and looked up and saw Robin standing there.
“Are you all right?” she asked through his closed car door.
He nodded. “Yeah, I’m all right.” He replied dejectedly.
She knocked again on his window. “Open up.”
Without thinking he opened his car door.
“Hi Chad,” she said. “I saw you struggling with something and I just thought I should check.”
He nodded to her again. But instead of answering he suddenly just laid his head against his steering wheel. “I’m not having the best of days,” he told her.
She didn’t say anything, but just stood there, waiting for him. Finally she asked quietly. “Are you going to show me what you’re wearing?”
Chad sat back in his seat. Knowing there was no avoiding it, he swung his legs out of the car. His one foot with the sock on it looked all too obvious in the bright morning light.
“What are you doing?” she asked.
“I was trying to cover up my pantyhose with these socks,” he explained, “but now I can’t get my shoes back on!”
She looked back at his feet. He hadn’t been wearing women’s shoes yesterday, but obviously he was today. “I don’t think you can wear those socks with those shoes,” she said. “And they don’t match anyway. Why would you want to?”
Chad just groaned and reached down and pulled his one sock off with a swift pull and threw it angrily onto the floor on the passenger side. Then he found his other shoe that was still off and slipped it on.
“There,” Robin said, “that looks much better. Ready to go to work now?”
Knowing that it was inevitable, Chad reached over and grabbed his purse. He opened it and pulled his cell phone out, then he grabbed his keys from the ignition and put his purse back on the seat again.
“Why don’t you carry it?” she asked.
Chad’s reply was filled with frustration. “Because this is all humiliating enough! That would only make it worse!”
“Then why are you doing it?” Chad didn’t answer. Instead he got out of his car and slammed his door shut.
“Oh for heaven’s sake!” Robin said. “Carrying a purse with the way you’re dressed right now can’t be that much worse! Grab the thing and get it over with!”
Almost angrily, he reopened his car door and grabbed his purse. Then he closed and locked the door. “Satisfied?” he asked with more annoyance than he should have.
“It’s not me who needs to answer that,” she said as she started walking towards the building.
Chad fell in beside her, feeling all the more foolish today about the way he was dressed than he did yesterday. “Sorry,” he said softly to her.
“Your purse looks a little heavy,” she noted. “What have you got in there?”
“All my makeup,” he replied.
“I noticed your eyes this morning.”
Chad grunted. “I’ll wash it off as soon as I get inside.”
“Why bother?”